August 20, 2026

Shannon Flanagan: Your Soft Skills Are Now Your Superpower | Ep 1309

In this episode of The Digital Executive Podcast, host Brian Thomas sits down with Shannon Flanagan, founder and CEO of Retail Women in Tech, to make a case that the most important thing missing from most AI transformation efforts isn't better technology — it's the right people in the room. Shannon opens with a career that started at 18 folding jeans and evolved through merchandising, consulting at Accenture, and leadership roles at Gap, Lands' End, and Macy's, shaped throughout by a single question she discovered at 25: what does it take to create the conditions where people love what they do every day? That question led her to organizational design, change management, and eventually to founding a nonprofit she describes as the hardest, poorest, and most fulfilling chapter of her life. She built Retail Women in Tech not to create another exclusive senior women's network, but to get more women — at every level, function, and age — into the rooms where AI decisions are being made, because she believes the qualities women have historically been told to downplay are exactly the ones the AI era will reward most. On change management, Shannon introduces a framework as simple as it is powerful: potential minus interference equals performance, and argues that most AI transformations fail because leaders lead with technology and ROI instead of starting with human readiness, trust, and psychological safety. She closes with a forward-looking vision of what success will look like in retail and beyond — not functional expertise, but judgment, discernment, ethics, and connection — and a challenge to women entering the field to stop waiting until they feel ready for AI roles and start recognizing that what they bring is exactly what the future needs. If you liked what you heard today, please leave us a review - Apple or Spotify.  Learn more about your ad choices. Visit megaphone.fm/adchoices

Also available on Apple Podcasts ↗